When presented with a complex new visual stimulus, viewers unfold an information sampling strategy which through a series of fixations and saccades provides them with the information they require given the task at hand. When that task is only loosely structured, as is the case when one is asked for an aesthetic appreciation of an unknown work of art, there is no single “best” location to send the eye to next. Under these conditions, scanpaths may be shaped by featural saliency, by systematic oculomotor biases, by image composition or by an active search for elements that allow aesthetic judgment. In the present study, we have attempted to assess the relative impact of these various determinants by asking art novices and art experts to evaluate a series of drawings (“Kalligrafie” by Anne-Mie Van Kerckhoven). During their inspection, eye movements were registered and afterwards measures of appreciation and evaluation were collected. Repeated stimulus exposure and presence vs. absence of an explanation of the artist's modus operandi were used to assess the effects of episodic and semantic experience with the viewed drawings. Scan paths were analyzed by means of fixation dispersion, fixation duration and fixation sequence measures. The obtained profiles were related to aesthetic judgments in order to determine whether different ways of looking at a work of art explain differences in judging it. In addition, the observed scan paths were compared to predictions made on the basis of featural saliency models, oculomotor bias models, and artist-defined region-of-interest models. Results indicated that art expertise mediates the predictive validity of these models of eye guidance when viewing art, and that parameters of scan paths allow predictive inferences about the aesthetic judgments that follow them.